CN111040777B - Liquid crystal composition and display element thereof - Google Patents
Liquid crystal composition and display element thereof Download PDFInfo
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/44—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing compounds with benzene rings directly linked
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- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
- C09K19/46—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40 containing esters
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- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/0403—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems
- C09K2019/0407—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit the structure containing one or more specific, optionally substituted ring or ring systems containing a carbocyclic ring, e.g. dicyano-benzene, chlorofluoro-benzene or cyclohexanone
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Abstract
The liquid crystal composition with negative dielectric anisotropy comprises at least one compound selected from general formula I as a first component, the mass content of the compound is 1-30%,
wherein R is linear alkyl and alkoxy with carbon number of 1-9, and alkenyl with carbon number of 2-7; z is a single bond, -CH2CH2‑，‑CH2O-; ring A is a benzene ring or cyclohexane, cyclohexene, where the hydrogen on the benzene ring may be substituted by 1 or more fluorine atoms. The liquid crystal composition has the characteristics of wide liquid crystal phase region, higher dielectric constant and lower rotational viscosity, and is suitable for TFT liquid crystal display, particularly liquid crystal display modes such as IPS (in-plane switching) mode, FFS (fringe field switching) mode and the like.
Description
Technical Field
The invention belongs to the technical field of liquid crystal materials, and particularly relates to a liquid crystal composition and a display element thereof, which are mainly used for a liquid crystal display.
Background
The liquid crystal display has the advantages of flat panel, low power consumption, light weight, no radiation and the like, and is rapidly developed in the field of information display. The liquid crystal display uses the characteristics of optical anisotropy and dielectric anisotropy of a liquid crystal material to realize a display function. The display modes are classified into Twisted Nematic (TN), Super Twisted Nematic (STN), dynamic scattering mode (DSP), thin film transistor driving mode (TFT), and the like. The TFT liquid crystal display can realize full color, high resolution, wide viewing angle, fast response, etc., has been widely used, and is the most important display technology in the current market.
The liquid crystal material for liquid crystal display has a nematic phase within a temperature range of the use environment, generally within a temperature range of-20 ℃ to +70 ℃ or more; meanwhile, the liquid crystal material must have high chemical stability, low viscosity, and suitable application of liquid crystal physical properties such as birefringence, dielectric anisotropy, resistivity and the like. One liquid crystal compound cannot meet all use conditions, and several or even more than ten liquid crystal compounds are compounded to form a mixed liquid crystal material, so that the practical use requirements of a display device can be met.
In the TFT liquid crystal display technology, depending on the liquid crystal alignment method, the liquid crystal display technology can be divided into several modes such as Twisted Nematic (TN), in-plane switching (IPS), Fringe Field Switching (FFS), and vertical alignment VA. The TN mode uses a dielectric anisotropy Δ ε (Δ ε ═ ε)∥－ε⊥) A liquid crystal material that is positive; the VA mode uses a liquid crystal material whose dielectric anisotropy Δ ∈ is a negative value; in the IPS and FFS modes, a liquid crystal material having a positive dielectric anisotropy Δ ∈ or a liquid crystal material having a negative dielectric anisotropy Δ ∈ may be used. For the FFS mode, a liquid crystal material having a negative anisotropy Δ ∈ can be used, and a higher light transmittance can be obtained than a liquid crystal material having a positive anisotropy Δ ∈. With the continuous improvement of the resolution of the display panel, the integral light transmittance of the liquid crystal device is reduced; the dielectric constant is therefore negative (Δ ε)<0) The liquid crystal material has the advantages ofAnd (4) good advantage. Meanwhile, the optimization of the response speed of the liquid crystal display device is also a technical problem, and the development of a liquid crystal material with low rotational viscosity is required continuously.
Liquid crystal compounds of negative dielectric anisotropy obtained by introducing fluorine atoms at the 2, 3-positions of the benzene ring are disclosed in a paper entitled "New liquid-crystalline compound with negative dielectric anisotropy, 1989, 5(1): 159-170".
In "New Liquid-Crystal Materials for Active Matrix Displays with New reactive digital analysis and Low volatile Viscosity.Jpn.J.Appl.Phys.,2000,39(11): L1180-L1182. ", discloses more detailed performance parameters for negative dielectric anisotropy liquid crystals. Wherein the liquid crystal compound based on 2, 3-difluoro-4-ethoxybenzene has a large value of delta epsilon but a value of rotational viscosity (. gamma.)1) And also large, adversely affecting the response speed.
US2002014613a1 discloses liquid crystal compositions having negative dielectric anisotropy, but suffer from the disadvantage of a relatively high rotational viscosity.
Disclosure of Invention
Aiming at the requirements of IPS, FFS mode and VA mode liquid crystal display technologies on a liquid crystal composition with quick response and high light transmittance, the invention aims to provide a novel liquid crystal composition with negative dielectric anisotropy and low rotational viscosity.
In order to realize the task, the invention adopts the following technical solution:
a liquid crystal composition having negative dielectric anisotropy, characterized by comprising at least one compound selected from the group consisting of compounds of the general formula I as a first component in an amount of 1 to 30% by mass, preferably 3 to 25% by mass, more preferably 5 to 20% by mass.
Wherein R is linear alkyl and alkoxy with carbon number of 1-9, and alkenyl with carbon number of 2-7; z is a single bond, -CH2CH2-，-CH2O-; ring A is a benzene ring or cyclohexane, cyclohexene, where the hydrogen on the benzene ring may be substituted by 1 or more fluorine atoms.
The liquid crystal compound shown in the general formula I has no polar substituent group in the lateral direction of a benzene ring, but unexpectedly shows remarkable negative dielectric anisotropy, and has extremely low rotational viscosity and moderate birefringence. The liquid crystal composition disclosed by the invention has the advantages that the liquid crystal compound shown in the general formula I is used as the first component, so that the liquid crystal composition has larger negative dielectric anisotropy, the rotational viscosity is reduced, and the response speed of a display device is favorably improved.
The liquid crystal compounds of the invention of the general formula I are preferably selected from the following structures:
the liquid-crystalline compounds of the formula I according to the invention are further preferably selected from the following structures:
the second characteristic of the liquid crystal composition of the present invention is that at least one compound selected from the group consisting of compounds represented by the general formula II as a second component is contained in an amount of 30 to 80% by mass, preferably 35 to 75% by mass, more preferably 40 to 70% by mass,
wherein R is1,R2Is linear alkyl group with carbon number of 1-9, alkoxy group, or alkenyl group with carbon number of 2-7; wherein Z1，Z2，Z3Is a single bond, -CH2CH2-，-CH2O-; the ring A, the ring B and the ring C are benzene rings or cyclohexane, cyclohexene and tetrahydropyrane, wherein hydrogen on the benzene rings can be substituted by 1 or more fluorine atoms; n and m are 0 or 1.
The liquid crystal compound shown in the general formula II has a 2, 3-difluoro substituent in the lateral direction of a benzene ring, and has larger negative dielectric anisotropy and higher clearing point.
The liquid crystal compounds of the general formula II according to the invention are preferably selected from the following structures:
the liquid-crystalline compounds of the general formula II according to the invention are further preferably selected from the following structures:
the third characteristic of the liquid crystal composition of the present invention is that at least one compound selected from the group consisting of compounds represented by the general formula III is contained as the third component in an amount of 10 to 70% by mass, preferably 20 to 60% by mass, and more preferably 30 to 50% by mass.
Wherein R is1,R2Is linear alkyl group with carbon number of 1-9, alkoxy group, or alkenyl group with carbon number of 2-7; wherein Z1,Z2Is a single bond, -CH2CH2-, -CH ═ CH-; the ring A, the ring B and the ring C are benzene rings or cyclohexane and cyclohexene, wherein hydrogen on the benzene rings can be substituted by 1 or more fluorine atoms; n and m are 0 or 1.
The liquid crystal compound shown in the general formula III has dielectric anisotropy of about 0, belongs to a dielectric neutral compound, and has a higher clearing point and a lower rotary viscosity.
The liquid-crystalline compounds of the general formula III according to the invention are preferably selected from the following structures:
the liquid crystal composition can also comprise one or more chiral additives, and the content is 0.01-1%; preferably 0.1% to 0.5%. The chiral additive is preferably selected from the following structures:
the liquid crystal composition also comprises a plurality of hindered phenols as antioxidant stabilizers, and the content of the hindered phenols is 1ppm-2000 ppm; preferably from 10ppm to 1000 ppm. The antioxidant stabilizer is preferably selected from the following structures:
the liquid crystal composition also comprises one or more ultraviolet light stabilizers with the content of 1ppm to 2000 ppm; preferably from 10ppm to 1000 ppm. The ultraviolet light stabilizer is preferably selected from the following structures:
the invention may also comprise one or more liquid crystal (RM) components having polymerizable groups, having the general structural formula iv:
wherein the ring A, the ring B and the ring C can be benzene ring or aromatic heterocycle, wherein the benzene ring can be substituted by 1 or more fluorine atoms; z1,Z2Is a single bond or an alkyl or alkoxy chain having 1 to 7 carbon atoms; p is a polymerizable group including an acrylate group, a methacrylate group; wherein the mass content of the polymerizable liquid crystal is 0.01-1%; preferably 0.05 to 0.5%. The polymerizable liquid crystal component is preferably selected from the following structures:
the liquid crystal composition has negative dielectric constant, lower rotational viscosity and higher response speed, and is suitable for TFT liquid crystal display technology, especially IPS, FFS, VA, PSVA and other modes.
Detailed Description
The present invention will be described in further detail with reference to specific examples.
The preparation method of the liquid crystal formula comprises the following steps: a thermal dissolution method is used. Firstly, weighing monomer liquid crystals with different weight proportions by using a precision balance, heating to 60-100 ℃, and stirring and mixing for 1-2 hours to uniformly dissolve all components. Cooling, filtering, degassing the filtered liquid in high vacuum (less than or equal to 100Pa), and packaging with high-purity nitrogen to obtain the target mixed liquid crystal.
Unless otherwise specified, the liquid crystal compositions according to the invention are prepared according to this process.
And testing the physical property and the photoelectric property of the mixed liquid crystal. The detailed test method of the physical property and the photoelectric property comprises the following steps:
(1) clearing point (Tni):
the polarizing hot stage method: the liquid crystal sample was coated on a glass slide and placed in an orthogonal polarization microscope hot stage with a temperature rise rate of 2 ℃/min. And observing the temperature at which the liquid crystal sample turns black from a bright state in a polarizing microscope, namely the clearing point.
Or by differential scanning calorimetry: the heating rate was set at 2 ℃/min under nitrogen atmosphere.
(2) Low temperature storage temperature (LTS): about 1mL of the mixed liquid crystal was put into a transparent glass bottle and placed in a low-temperature refrigerator. The temperature is set to-20 ℃, 30 ℃ and 40 ℃, and the mixture is stored for 10 days respectively, and whether crystal precipitation or smectic phase exists is observed. If no crystal is precipitated at the temperature of minus 30 ℃, LTS is less than or equal to minus 30 ℃.
(3) Birefringence (Δ n): respectively measuring ordinary rays (n) by using Abbe refractometer and a light source of 589nm at the constant temperature of 25 DEG Co) And extraordinary ray (n)e) Refractive index of (1), birefringence (Δ n) being equal to ne－no。
(4) Dielectric constant (Δ ∈): and (3) testing by using an LCR (liquid crystal resistance) meter at the constant temperature of 25 ℃. Δ ε ═ ε∥-ε⊥I.e. the dielectric constant (. epsilon.) in the direction of the molecular long axis∥) Dielectric constant (. epsilon.) with respect to the minor axis of the molecule⊥) The difference of (a).
(5) Spring constant (K)11，K33): under the constant temperature condition of 25 ℃, K is obtained by testing a liquid crystal capacitance-voltage (C-V) curve and fitting11And K33。
(6) Rotational viscosity (. gamma.)1): under the constant temperature condition of 25 ℃, the transient current value Ip of the liquid crystal molecules deflected along with the movement of the electric field is tested by applying voltage to the liquid crystal test box, and the rotational viscosity gamma is calculated1。
The performance of the monomer liquid crystal was tested by dissolving it in the following basic formulation (Host). The property parameters of the monomers, e.g. clearing point, Δ ε, Δ n, γ1Calculated by extrapolation. The basic formula (Host) is prepared from the following three liquid crystal compounds according to the mass ratio of 1:1: 1.
Code number and description:
(1) physical parameters
| (Code) | Description of the invention | Unit of |
| Tni | Clearing points | ℃ |
| TCN | Low temperature storage temperature | ℃ |
| ε⊥ | Dielectric constant perpendicular to director | |
| ε∥ | Dielectric constant parallel to the director | |
| Δε | Dielectric anisotropy | |
| Δn | Double refractive index | |
| γ1 | Rotational viscosity | mPa·s |
| K11 | Elasticity constant of splay | pN |
| K33 | Flexural elastic constant | pN |
(2) Structural abbreviations
For example:
liquid crystal phase transition temperature: c represents melting point, S represents smectic phase, N represents nematic phase, and Iso represents liquid state.
Example 1
Synthesis of 4- (4-propyl-cyclohexyl) -1- (2-fluoroethoxy) benzene (3CPO2F)
The synthetic route is as follows:
in a 500ml three-necked flask, 21.8g of 4- (4-propyl-cyclohexyl) phenol, 27.6g of potassium carbonate, 14.2g of 2-fluoroethanol methanesulfonate, and 300ml of N, N-dimethylformamide were charged, and the mixture was heated to reflux for 5 hours. The temperature was reduced to room temperature, 300ml of water was added, and 200ml of toluene was extracted. The extract was washed with water to neutrality, toluene was removed to give an oil, which was recrystallized from absolute ethanol to give 21.7g of white crystals, yield 82%, and chromatographic purity 99.9%.
And (3) structural identification:1HNMR(CDCl3，500MHz)δ：0.83(t，3H，J＝7.5Hz)，0.92-0.98(m，2H),1.15-1.45(m，7H)，1.76-1.80(m，4H),2.31-2.37(m，1H),4.12(dt,2H,J1＝15Hz,J2＝5Hz)；4.66(dt,2H,J1＝25Hz,J2＝5Hz),6.78(d，2H，J＝5Hz)，7.06(d，2H，J＝5Hz)。
MS(70eV)m/z(％)：264.3(55，M+)，179.2(100)，166.1(30)。
and (3) testing thermal performance: c59 Iso.
The mixture is added into a basic formula according to the proportion of 10% to test physical performance parameters, and the physical performance parameters obtained by extrapolation calculation are as follows: Δ ∈ -2.2, Δ n ═ 0.0792, γ1＝-14mPa·s，Tni＝-8.6℃。
Example 2
Synthesis of 4- (2-fluoroethoxy) -4' -propylbiphenyl (3PPO2F)
The synthetic route is as follows:
4- (2-Fluoroethoxy) -4 '-propylbiphenyl was prepared in the same manner as in example 1, except that 4- (4-propyl-cyclohexyl) phenol was replaced with 4' -propylbiphenol.
And (3) structural identification:1HNMR(CDCl3，500MHz)δ：0.90(t，3H，J＝7.5Hz)，1.56-1.64(m，2H)，2.54(t，2H，J＝10Hz),4.18(dt,2H,J1＝15Hz,J2＝5Hz)；4.73(dt,2H,J1＝25Hz,J2＝5Hz),6.92(d,2H,J＝7.5Hz)，7.15(d,2H),7.38(d，2H)，7.41(d，2H)。
MS(70eV)m/z(％)：258.3(80，M+)，229.2(100)。
and (3) testing thermal performance: C90S111 Iso.
Physical properties:Δε＝-2.9，Δn＝0.1472，γ1＝67mPa·s，Tni＝17.6℃。
examples 3 to 5
The same procedure as in example 1 was repeated except for using 4- (4-propyl-cyclohexyl-1-enyl) phenol, 4- (4-vinyl-cyclohexyl) phenol, and 4- (2- (4-propylcyclohexyl) ethyl) benzene instead of the 4- (4-propyl-cyclohexyl) phenol in example 1, respectively, to prepare:
example 6
The liquid crystal composition has the following components in mass ratio and performance data:
example 7
The liquid crystal composition has the following components in mass ratio and performance data:
example 8
The liquid crystal composition has the following components in mass ratio and performance data:
example 9
The liquid crystal composition has the following components in mass ratio and performance data:
example 10
The liquid crystal composition has the following components in mass ratio and performance data:
example 11
A polymer stabilized liquid crystal composition comprising the composition of example 8 in an amount of 99.7%; and a polymerizable compound (RM) represented by the following formula in an amount of 0.3%,
devices comprising the composition can form a stable polymer layer upon UV exposure.
Comparative example 1
The liquid crystal composition has the following components in mass ratio and performance data:
the composition of comparative example 1 replaced the 3CPO2F component of example 7 with the conventional liquid crystal compound 3CPO 2; 3CPO2F has the same molecular backbone as 3CPO2 except that the terminal alkoxy fluorine atom is substituted. The physical property data show that the example 7 has a larger negative dielectric anisotropy value and a significantly reduced rotational viscosity compared with the comparative example 1, and is beneficial to improving the response speed of the liquid crystal display element.
Claims (6)
1. A liquid crystal composition characterized by comprising as a first component at least one compound selected from the group consisting of compounds of the general formula I in an amount of 1 to 30% by mass,
wherein R is linear alkyl and alkoxy with carbon number of 1-9, and alkenyl with carbon number of 2-7; z is a single bond, -CH2CH2-，-CH2O-; ring A is benzene ring or cyclohexane, cyclohexene, wherein the hydrogen on the benzene ring can be substituted by 1 or more fluorine atoms;
and at least one compound selected from the group consisting of compounds represented by the general formula II as a second component, in an amount of 30 to 80% by mass,
wherein R is1，R2Is linear alkyl group, alkoxy group with carbon number of 1-9, or alkenyl group with carbon number of 2-7;
Z1，Z2，Z3is a single bond, -CH2CH2-，-CH2O-; ring A, ring B and ring C are benzene rings or cyclohexane, wherein hydrogen on the benzene rings can be substituted by 1 or more fluorine atoms; n, m is 0,1, 2;
and at least one compound selected from the group consisting of compounds represented by the general formula III as a third component in an amount of 10 to 70% by mass,
wherein R is1，R2Is linear alkyl group, alkoxy group with carbon number of 1-9, or alkenyl group with carbon number of 2-7; z1，Z2Is a single bond, -CH2CH2-，-CH＝CH-; ring A, ring B and ring C are benzene rings or cyclohexane, wherein hydrogen on the benzene rings can be substituted by 1 or more fluorine atoms; n is 0,1, 2.
2. The liquid crystal composition of claim 1, wherein the compound of formula i is selected from one of the following structures:
3. the liquid crystal composition of claim 1, wherein the compound of formula ii is selected from one of the following structures:
4. the liquid crystal composition of claim 1, wherein the compound of formula iii is selected from one of the following structures:
5. the liquid crystal composition according to claim 1, further comprising one or more polymerizable compounds represented by the general structural formula IV, wherein the polymerizable compounds are contained in an amount of 0-1% by mass:
wherein ring A, ring B, ring C are benzene rings, wherein H on the benzene ring may be substituted with 1 or more fluorine atoms; z1,Z2Is a single bond or an alkyl or alkoxy chain having 1 to 7 carbon atoms; p is an acrylate groupAnd a methacrylate group.
6. A liquid crystal display element comprising the liquid crystal composition according to any one of claims 1 to 5.
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| EP0315370A2 (en) * | 1987-11-04 | 1989-05-10 | Sumitomo Chemical Company, Limited | Ether compounds and their production, and insecticidal and/or acaricidal compositions containing them |
| DE4315371A1 (en) * | 1993-05-10 | 1994-11-17 | Merck Patent Gmbh | Benzene derivatives, and liquid-crystalline medium |
| DE4338164A1 (en) * | 1993-11-09 | 1995-05-11 | Merck Patent Gmbh | Process for the preparation of substituted 2,2-difluoroethoxybenzene |
| EP0727428A1 (en) * | 1995-02-13 | 1996-08-21 | Shin-Etsu Chemical Co., Ltd. | Novel silacyclohexane compounds, preparation thereof, liquid crystal compositions comprising the same, and liquid crystal devices comprising the compositions |
| US5589102A (en) * | 1994-09-06 | 1996-12-31 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Benzene derivatives, and liquid-crystalline medium |
| CN104087312A (en) * | 2014-06-17 | 2014-10-08 | 北京八亿时空液晶科技股份有限公司 | Liquid crystal composition and its application |
| CN109207159A (en) * | 2017-06-30 | 2019-01-15 | 北京八亿时空液晶科技股份有限公司 | A kind of liquid-crystal compounds of negative dielectric anisotropic and the preparation method and application thereof |
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| EP0315370A2 (en) * | 1987-11-04 | 1989-05-10 | Sumitomo Chemical Company, Limited | Ether compounds and their production, and insecticidal and/or acaricidal compositions containing them |
| DE4315371A1 (en) * | 1993-05-10 | 1994-11-17 | Merck Patent Gmbh | Benzene derivatives, and liquid-crystalline medium |
| DE4338164A1 (en) * | 1993-11-09 | 1995-05-11 | Merck Patent Gmbh | Process for the preparation of substituted 2,2-difluoroethoxybenzene |
| US5589102A (en) * | 1994-09-06 | 1996-12-31 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Benzene derivatives, and liquid-crystalline medium |
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